Water → 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine

HRID 440008Notes

Reaction equation

HRID 440008 reaction equation
[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.B#B.CSC.O.[OH-].[Na+]>O1CCCC1>[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 123593406,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-oneHCID 22038413Diborane dimethylsulfide

Product 1

HCID 123593416,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepineYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.070 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-one in 2 ml of tetrahydrofuran is added 0.45 ml of a 2.0M solution of diborane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 3 hours, poured into water and make basic with 2N NaOH. The tetrahydrofuran is removed under vacuum and the residual aqueous mixture extracted with diethyl ether. The extract is washed with brine, dried (Na2SO4) and the solvent removed to give 0.065 g of a colorless oil; one spot by thin layer chromatography (silica gel) with ethyl acetate-hexane (1:2) as solvent (Rf 0.81).

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customThe tetrahydrofuran is removed under vacuum
  3. extractionthe residual aqueous mixture extracted with diethyl ether
  4. washThe extract is washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-0b66e98dcc514fcfa12e1a18107dc7e3
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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